N-Methoxy-N-methylnicotinamide → 1-(Pyridin-3-yl)butan-1-one

HRID 1661554Notes

Reaction equation

HRID 1661554 reaction equation
CN(OC)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[CH2:13]([Mg]Cl)[CH2:14][CH3:15]>C1COCC1>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:3](=[O:10])[CH2:13][CH2:14][CH3:15])[CH:5]=1

Participants

4

Reactant 2

HCID 10558996N-Methoxy-N-methylnicotinamideHCID 178455855HCID 178455855, compound

Product 1

HCID 4595021-(Pyridin-3-yl)butan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask is charged with N-methyl-N-methoxy-nicotinamide (1.0 g, 6.02 mmol) and THF (10 mL). Propyl magnesium chloride (2M in THF, 3.31 mL, 6.62 mmol) is added and the mixture is stirred at room temperature overnight. It is quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. The combined organic layer is dried over sodium sulfate and concentrated in vacuo to afford 1-pyridin-3-yl-butan-1-one as a yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.03 (t, J=7.5 Hz, 3H), 1.74-1.87 (m, 2H), 2.97 (t, J=7.3 Hz, 2H), 7.42 (dd, J=8.0, 4.9 Hz, 1H), 8.24 (dt, J=8.0, 2.0, 1.9 Hz, 1H), 8.78 (dd, J=4.9, 2.0 Hz, 1H), 9.18 (d, J=2.0 Hz, 1H).

Workup

  1. customIt is quenched with saturated sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layer is dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b1dd263df0d43eeafd82ba277009206
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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